ChemInform Abstract: A Highly Stereoselective Synthesis of D-Erythrose Derivatives by One-Carbon Homologation of 2,3-O-Isopropylidene-D-glyceraldehyde with (R)-Methyl p-Tolyl Sulfoxide.

1. Arroyo-Gomez, Y. ¹
2. Rodriguez-Amo, J. F. ¹
3. Santos-Garcia, M. ¹
4. Sanz-Tejedor, M. A. ¹

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DOI: 10.1002/CHIN.200024201 GOOGLE SCHOLAR lock_openOpen access editor

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Abstract

Aldehyde (VI) is prepared in three steps with 50% overall yield via sulfoxide (III) which is obtained by the title reaction with ¿98% diastereoselectivity. Pummerer rearrangement of benzyl protected sulfoxide (Va) with (CF3-CO)2O/lutidine followed by work-up with aq. NaHCO3 gives the target compound in quantitative yield. The Pummerer rearrangement of (Va) with NaOAc/Ac2O and subsequent treatment with iBu2AlH affords aldehyde (VI) in only 60% yield. Pummerer rearrangement of (Vb) with NaOAc/Ac2O leads to an epimeric mixture of S-ketals (IX) with replacement of the Tms by the acetyl group.

Bibliographic References

• Arroyo-Gomez, (2000), Tetrahedron: Asymmetry, 11, pp. 789, 10.1016/S0957-4166(00)00005-7